The Second Date
by mistycaribbeanflowers
Summary: "Serena...I have something I want to talk about with you. I don't know how to say it and this is probably going to be very awkward, but just promise to hear me out, okay?" All function in Serena's body came to a screeching halt. Ash was scratching the back of his neck. She knew better than anyone that it meant he was nervous. This was it. Oh sweet Mew, it was happening.
1. Chapter 1

**Hello, hello!**

 **I've had a million and one ideas floating around my head lately, so I've been working away at some. I decided this would be the first I posted.**

 **This is my first chapter fic, so I'm a little nervous.**

 **But anywho, here I present to you _The Second Date._ I won't give anything away, but be forewarned that this story can go any way and where it ends up going may surprise you.**

 ** _Ash: 20_**

 ** _Serena: 19_**

 **Disclaimer: I do not own Pokemon or any of its characters.**

 **Enjoy!**

* * *

 _ **Saturday: Lumiose City. 11:35 AM; Present**_

Serena was practically gliding down the busy Lumiose street. Had she not totally been on cloud nine, she would've noticed the attention she was drawing and probably would've pulled herself together.

"Miss? Miss, are you quite alright? Are you lost? Oh, Gilles, she looks positively unwell, we should do something..." An elderly couple, concerned for her well-being. She didn't respond.

To some who watched, she looked like a graceful Kirlia, swept up in a dreamy melody. Beautiful to watch, but hardly suitable for a city sidewalk. People bumped into the honey haired woman, left and right. And each time it happened she barely batted an eyelash.

"Hey, move it _toots!_ Some of us cant afford to wander around, you know!" A gentleman dressed in business attire that she nearly _slammed_ into, just shook his head in disgust; there was something about happy-go-lucky tourists that always ruined his day.

But little did he know, she was well acquainted with these streets.

It had been two whole years since she'd been in Lumiose City and she missed it with every fiber of her being. While early summer was always gorgeous in her humble countryside hometown of Vaniville, it never quite compared to the beauty of Lumiose City. The already lively city was now covered in the aroma of honeysuckle and lavender. It was hands down, Serena's absolute favorite time of year. And she suspected it had to be everyone else's as well.

She snickered to herself.

Well perhaps not everyone.

She remembered Clemont always complained about the warm air making his jumpsuit itchy. It was a shame too. He would look really nice if he decided to try a nice weather appropriate ensemble now and then. It would no doubt make the blond man uncomfortable, but it would definitely enhance his style tenfold. She made a note to help him out with that one day when she wasn't fulfilling Kalos Queen duties.

Serena stopped at a cross light, waiting for her chance to cross.

And then it hit her.

For once, she wasn't rushing to get anywhere. And it felt absolutely _wonderful._

Since becoming a Kalos Queen around four years ago, Serena's life was beyond hectic. She was needed for special appearances and performances at showcases. A lot of times, those requests came at a moments notice-leaving her very little time to really prepare for it. Other times, she was asked to appear at some of the trainer academies and tell them all about her exciting career. She was even scouted by designers to model their latest designs and be the face of their ad campaigns. Though, she really didn't mind that last one too much...

Her influence wasn't just limited to a pretty figure head. No, she was a source of spirit for trainers everywhere. She was invited to the Kalos League opening rally last year to light the flame of Moltres, a very important Pokémon League tradition. And she wasn't even a competitive battler!

Serena was a symbol of her region and people.

 _Her_.

Serena. The one who started her journey without a dream or goal of her own.

People were inspired by _her_ and it was something that humbled her greatly, every single day.

However, that meant she barely had time for herself, let alone any of the people she loved.

It was why she was extra excited to see her three closest friends today. She could barely contain the giant grin on her face. She hadn't seen Clemont and Bonnie for two whole years, and Ash a whopping four. It was really killing her that they'd gone so long without any real face to face contact. She somewhat regularly communicated with Clemont, be it over the phone or through some texts. Bonnie called her from Pokémon centers whenever she could.

But Ash?

Ash was a whole side of the world away. And no matter how busy she got, she always spared a moment to think about her handsome friend.

Right after his loss in the Kalos League, Ash went on a training retreat. No one had heard from him for nearly a year. She called his mother several times, but even Delia was unaware of her son's whereabouts. And much to Serena's chagrin, the older woman barely batted an eyelash, claiming that Ash was fine and that there was nothing to worry about. Naturally, Serena and Clemont feared for the worst.

Luckily, their worries were put to rest when Ash was reported as a competitor in the Indigo League; the first ever Pokémon League he participated in. Ash always mentioned that he wished he could've done better back in his first stint; his inexperience as a trainer definitely played a role in his loss. But he never gave into self deprecation, assuring himself that he was meant to continue training and get stronger. He would make his dreams of being a Pokémon Master happen when the time was right.

And he did.

The Pride of Pallet had gone the distance and won the League and was the Kanto Champion.

Serena remembered seeing all of the photos and press coverage surrounding the boy. Ash practically broke the Pokémon world with his victory. Trainers wanted to be him and girls wanted to have his children. Ash still remained undefeated and his every waking moment was recorded, luckily for her. It was the only way she ever really got to see him. And while she found her friend attractive in their teenage years, he was downright gorgeous as a grown man.

" _A grown man that I definitely want to get all alone and …"_

Serena felt the heat rush to her cheeks. Her first instinct was to berate herself for having such scandalous thoughts, but she broke through that nagging voice that was so ready to put her down.

"No more sugarcoating, Serena. You're an adult with desires likes everyone else." She muttered to herself, taking deep breaths to calm herself. She crossed the street and continued straight ahead.

Four years later and she was still harboring unresolved love for a man who barely reacted to anything she did, let alone, showed any inkling of being remotely attracted to her! It was so damn frustrating.

But perhaps that was changing as well.

After all, it had been _Ash_ , the one who really never kept in contact with anyone, that had reached out to her.

 _Ash,_ who would sooner scarf down a cheeseburger and fries, initiated the plan for lunch today. At a _café_ , no less. _Her_ favorite café.

It meant something. And Serena was only too eager to find out.

* * *

Feel free to review and once again, constructive criticism is definitely appreciated!

I'll try to have the next chapter up as soon as possible. Being that the Thanksgiving holiday is upon us, which means family/friends and all that crap, I will definitely try to focus.

Happy, healthy and safe Thanksgiving to everyone who celebrates!

~mistycaribbeanflowers


	2. Chapter 2

Hello again, all!

I want to thank you all for your reviews (which were very friendly) and the favorites. You really know how to make a gal feel special! I hope that I can keep doing this justice. I know the first chapter was a little short, so I tried to make this one a little longer.

So without further ado, here is the second installment of The Second Date.

Disclaimer: I do not own Pokemon or any of its characters.

~Enjoy

* * *

 _ **Tuesday: Laverre City. 12:00 PM. Earlier that week.**_

"Don't forget to tend to the skirt. It must not obstruct her feet. The last thing we would want is for our lovely model to fall and injure herself!" Barked Cecile, a short, older woman with a grey pixie cut. Her beady eyes were narrowed.

"Oui!" A chorus of workers quickly replied; their head seamstress would not tolerate anything less than perfection. Cecile, pleased with their response, moved to the other side of the room to supervise.

Serena let out a sigh of relief. She wasn't even being spoken to, but the tension in the room was thicker than a Koffing's Smog attack. And she felt like she was choking on the residual effects.

" _Thank Arceus."_

She was standing on a raised platform in the middle of Valerie's posh studio, swarmed by tailors. She couldn't quite remember how many times she'd been in that very room, be it for alterations or quick changes, but the excitement always made it feel like her first time.

The Laverre City Gym Leader personally requested Serena to be the face of her brand new collection. It was dedicated to the beauty of fairy type Pokémon. Two days from now, The Kalos Queen would be walking down the runway with Sylveon at her side. As for the week after, photo shoot after photo shoot would be launched.

Valerie nearly went deaf after that phone call, but Serena's "yes" had been loud and enthusiastic, so the designer wasn't too offended. Three hours later, the blond woman had arrived at the gym and was immediately whisked away. It was long, repetitive process, but Serena was a trooper. She stood still, often being poked and prodded as each outfit was altered; there were more piles of clothing that hadn't been touched yet.

Even _Serena_ was overwhelmed. And she was positive no one around loved clothes nearly as much as she did.

Except maybe Dawn.

She smiled as she thought about the stylish blue haired coordinator Ash had introduced her to years ago. They truly were kindred spirits.

Serena looked at herself in the mirror. Valerie was no doubt a genius designer, but this had outdone anything she'd ever see the gym leader create.

It was a gorgeous floor length, satin gown. The top half of her gown was a soft yellow color, which would gradient into a beautiful pearl pink at the skirt. There were about four different tailors, vigorously hemming the massive skirt.

She felt like a princess preparing to meet the man of her dreams.

"Arielle, take in the top of that gown. Miss Valerie specifically asked for that one to be taken in!" Arielle's face twisted into confusion.

"But, why would Miss Valerie require such a thing?" Cecile, leaned in to Arielle's ear.

"That gown will be worn during the finale walk on the runway, so it is crucial that it fits perfectly. The Kalos Queen, though a wonderful asset to the collection, is…lacking the appropriate assets required to fill out the top." Serena frowned at the woman through the mirror.

In addition to lacking basic manners, it appeared Cecile wasn't very good at whispering.

Serena was well aware that she wasn't the among the chestiest of women out there. It really didn't bother the young woman. Cecile's tone of voice, however, was dripping with disdain and _that_ struck a nerve. It took a great deal to upset Serena, but the old Miltank seemed to be doing an excellent job of it.

Arielle nodded at Cecile and immediately cinched in the top, constricting the blond woman's air flow. Serena tried let out a breath, but to no avail. She started to tremble. Arielle looked up into the mirror and saw that Serena was turning slightly blue. Cecile went on the attack.

"Arielle, what have you done?! You're going to kill her!" Cecile screamed. Arielle immediately jumped into action and loosened the gown. The air rushed back into Serena's lungs causing her to hack. She fell forward, landing in Arielle's waiting arms.

"Miss Serena, are you okay?" Serena continued to cough. Cecile, turned to another tailor.

"Quick, get her water!" Emil, nodded and ran out of the room. Arielle led Serena over to a leather couch on the other side of the room.

"Oh! Miss Serena, I'm so sorry!" Emil ran back into the room and handed the water to Serena immediately, which she slowly downed. The color rushed back to her face and she breathed deeply. Cecile, knelt toward her.

"Queen Serena, are you quite alright? I would hate to know that this level of incompetence would result in your refusal to represent the collection." Serena noticed Arielle cower on her right.

"I'm fine, I promise," Serena turned to Arielle and smiled, "It's alright, Arielle, thank you." Arielle's face melted. Cecile huffed and cleared her throat.

The Kalos Queen stifled an eye roll; the seamstress seemed all too eager to kill the moment.

"Yes, well, Queen Serena, I'm sure after your ordeal, you would like a moment to collect yourself. We will reconvene in ten minutes." Before Serena could speak, Cecile ushered the other tailors out of the room to give her privacy.

Or, most likely, to harass them further. Serena decided it was a little of both.

Suddenly an upbeat pop song blared on the other side of the room, startling the woman out of her thoughts. She recognized it as her cell phone. Serena gathered up as much her skirt as she could and moved to other couch where her bag lay. She leaned down and shuffled through her bag, cursing herself for not cleaning it out beforehand. She had _entirely_ too much makeup in there.

"Ugh!" Serena huffed and turned her bag upside down. All of the contents came pouring out and on top of it sat her pink smartphone. Her eyes narrowed and she looked at the number flashing across the screen.

It wasn't a number the woman recognized. The area code wasn't even native to the Kalos Region.

"Well, that's weird." She didn't want to answer it. What if it was some creepy fan who'd somehow gotten her number? But then, again….

What if it was someone important? Like a director at Pokéstar Studios asking her to be in their next cult classic? She had been eyeing the role of Spinarak-Man's love interest for quite some time.

That slight possibility was all the encouragement she needed.

"Hello, this is Serena Yvonne speaking."

 _Static._

"Hey, Serena?" A deep voice answered back. It was a man. Serena blinked and looked at the phone in confusion. This person didn't sound familiar, nor did they have an air of importance, so she concluded it probably wasn't business related.

"Uh, yes? Who may I ask is calling?" The deep voice let out a chuckle.

"C'mon, Serena. I know it's been a while, but don't tell me you've forgotten me already!"

Serena froze. That raspy, yet playful, tone of voice.

" _No…it couldn't be.."_ But it was.

"Uh...Serena? You there? Hello?"

Serena was having trouble breathing. Emotions were coursing through her veins; shock, relief and most importantly, joy.

" _It's him. It's really him."_ The words ran over and over through her head, until the sound of his voice calling her brought her back. She found her voice.

"Ash! I can't believe it's actually you! What's going on? I've missed you so much." She cringed. That sounded way too eager.

" _Smooth move, Serena."_ Her conscience nagged at her. Luckily, Ash didn't seem to notice.

"I've missed you," She felt her former teenage self scream, "and Clemont and Bonnie, too!" With that she plummeted down to Earth.

Of course. It was too good to be true.

"...Yeah. Me too. So Ash, is there a particular reason you called?" Since he clearly wasn't going to confess any undying love for her. Not that she was really expecting him to. Ash was consistent, after all.

"Yep! I have a week off! The Indigo League is starting up in a week and a half, so I'm deciding to take a trip out to Kalos for a few days. I really want to see you guys! I was hoping we could try and grab some lunch in Lumiose on Saturday. You know, at that café you like so much? That is, if you aren't busy-"

"No, I'm not busy at all! Not even in the slightest! And I know Clemont and Bonnie won't mind pushing things aside too." Serena pounced on that offer immediately. It wasn't everyday Ash Ketchum came to visit and all unrequited love aside, she did truly miss her friend.

As for the two Lumiose siblings, Serena knew they wouldn't let anything stop them from meeting up with Ash. The Kalos League was currently underway, which meant all gyms were closed and Bonnie had just returned from trying her luck in the Hoenn League. She ranked Top 8, losing to some kid named Max Maple.

It couldn't have been a more perfect week to visit. Ash's excitement was practically pouring through the line.

"Awesome! I'll call and let them know the plan! See you Saturday, Serena!"

"Bye Ash, I can't wait! See you soon." The line went dead, but Serena was on a high.

Saturday couldn't come soon enough.

 **...**

 **...**

 _ **Saturday. Lumiose City. Time: 11:55 AM. Present.**_

She broke into a small trot, no longer able to contain herself. Hell, if Ash was being bold and taking the initiative to call her and tell her _he_ missed _her_ , perhaps he was feeling bold in other areas as well!

She pulled out all the stops for their meeting today at the small cafe. Today's ensemble would definitely bring out a reaction from the man.

Serena's white kitten heels clacked against the cobblestone. Her petite frame was covered by a sleeveless pale blue sundress. The dress had a tiered skirt, that ended at her mid. Her hair, which had grown a considerable amount from her short cut, was swept into a sleek ponytail. Her bright blue eyes were covered by white sunglasses to keep her identity hidden from the public. Her smiling lips were covered in a light pink gloss.

Serena was no doubt a beautiful young woman, but the most striking thing about her that day was the confidence radiating off of her.

Today was the day for sure.

She was going to have lunch with Ash Ketchum and maybe, if she played her cards right, he would be hers.

 ** _..._**

 ** _..._**

 _ **Saturday. Lumiose City. Café Électrique. 11:55 AM. Present**_

Ash sat in the corner of Café Électrique's backyard patio and despite the beautiful atmosphere, the Kanto Champion found himself rather tense.

Luckily for him, the quaint café valued privacy for their famous patrons and prepared accordingly. For today, the patio was enclosed by tall green shrubs that completely blocked out the view of inside from the street. An additional cabana was placed to further shield them from any other peering eyes. Pinot, the Maître d', assured Ash that he and his company would be in complete seclusion.

The raven haired man was grateful; it was one less worry. The last thing he wanted was to cause an uproar. He had a far more pressing matter to concern himself with.

Her name was Serena Yvonne.

He looked down at his Pokégear. The time read that it was five minutes until noon, but there was no sign of his friend anywhere. Ash wanted to kick himself. He should have anticipated that Serena would definitely be fashionably late, but it was making him antsy. Suddenly his device vibrated against the table. It was a text. Ash picked it up and looked at the message.

Thank goodness it wasn't Serena. He could deal with literally anyone else but her, at the moment.

"It means I have more time to figure this out." He muttered. He had no idea where to even start.

 _ **'Is everything okay?**_ _'_ Ash looked at the screen and typed his response.

 _ **'She's not here yet.**_ _'_ Ash craned his neck to look for the young woman. She still wasn't there.

 _ **'Oh.**_ _'_ Was the single response. His Pokégear beeped with another message.

 _ **'Are you nervous?**_ ' Ash snorted.

' _ **Is water wet?**_ '

' _ **Alright, alright, stupid question.'**_ Ash snickered. He felt himself relaxing a little. Another text quickly followed after.

' _ **Everything will be okay, Ash.'**_ The trainer's bit his lip.

' _ **Somehow, I'm not so sure.**_ **'** He really wasn't. It would either go really well or horribly wrong and that was enough to drive him up a wall. For the first time in years, Ash Ketchum was afraid to take the plunge and he found it disturbing. It was so unlike him.

The device started to ring and Ash answered it. He already knew who it was.

"Yeah?"

"You're freaking out over nothing." The voice said, jumping right to the point.

"Way to trivialize the issue at hand. You're such a good friend." He didn't need this right now.

"Wow, trivialize? That's some pretty serious word usage there. Are you sure you're Ash?"

"Good _bye_." Ash got ready to hang up.

"Okay, I'm done. No more jokes, I promise!" Ash put the device back to his ear.

"I'm just scared. I haven't seen her in years and I'm about to drop a bomb. How is she going to react to this? What if I catch her off guard?" He let out a shaky breath.

"Look, Ash, I get it. It's an uncomfortable situation, but you've been through way worse and frankly, I think being honest with a close friend is something you're more than capable of. I know you care about Serena, and from what I've seen, she definitely cares about you." All of it was true.

Serena was one of Ash's very good friends. Their friendship had only grown from that fateful day at Professor Oak's summer camp. Granted, they had been five year olds at the time; they had no way to interact because they lived on different sides of the world. But when they met again, they truly bonded.

No matter how today played out, he was positive that the blond woman wouldn't just throw away their relationship. They had been through far too many adventures together for that to happen.

"You're right. I can do this." Ash looked up and saw Pinot walking toward him. He informed the person on the other line of this, apologizing for cutting the call short.

"Alright, I'll let you go. Call me later and let me know how it went. The time difference is kind of a bitch, but for you, I _guess_ I'll manage." Ash chuckled at the tragic tone of voice his friend put on.

"Will do. Thanks a lot for the pep talk. In fact, it was such a good pep talk that you should direct some of this energy into being my cheerleader for my next tournament." He knew he was pressing buttons, but he couldn't resist.

"Not in this lifetime." Before Ash could respond the line went dead. He put down his Pokégear and glanced at the time. It was fifteen minutes past noon. Soon after, the Maître d' reached his table. The middle aged man stood tall, with little to no emotion on his face. Ash didn't hold it against him; he wouldn't smile if he was forced to wear a tux for work either.

"Monsieur Ketchum, I hope I am not interrupting." He suppressed a cringe. The Kanto Champion knew that Kalosians were well known for being formal, but it always made him a tad uncomfortable. His status hadn't changed who he was as a person. He was still just a guy from the countryside that loved Pokémon.

"Oh, not at all. I just hung up. Is everything okay? And, please, call me Ash." Pinot remained unaffected, staring blankly into Ash's eyes.

"Your dining companion has arrived Monsieur Ketchum. I wanted to inform you before I escorted her to you." Ash nodded his head.

"Thank you, so much. Please bring her back here."

"Oui. I will be back momentarily." Pinot walked away. Suddenly feeling self conscious about his appearance, Ash stood up and smoothed down his blue button down shirt. He held up his spoon and used it as a mirror, attempting to smooth down his unruly hair. Everyone knew he wasn't one for dressing up; his outfit was quite casual and comfortable. He was sure Serena would appreciate his effort, no matter how minimal it was.

A few moments later, he heard the click-clacking of heels against the cobblestone floor. The nerves made his stomach clench.

Why was he putting himself through this torture again?

Ash took a deep breath and tried to calm himself. He had to stay strong.

" _Take it easy. You care about her. That's why you're doing this."_ That was more than enough reason for him.

Pinot emerged first and Serena stepped into view behind him, the skirt of her dress bouncing in time with her steps. Her lips were fixed into a timid smile. He was slightly relieved. It meant Serena was probably just as nervous as he was.

They were finally face to face.

Ash felt his body relax. He stuffed down his nerves and smiled.

It was show time.

* * *

Okay! Once again, please please review. I would really love any and all feedback.

I can't say exactly when I'll update this, so once again, I won't make any guarantees. Why? Because finals, finals, finals, drowning is finals. I'm up to my neck in homework, final papers, final performances and whatnot. And then of course, Christmas and New Years and more people wanting a piece of me. But! I will try to have to ready as soon as I can.

Thank you once again and good luck to anyone with finals or hectic holiday season madness!

Merry Christmas, Happy Hanukkah, Happy Kwanza, Winter Solstice/Yule to all who celebrate!

And Happy New Year!

~mistycaribbeanflowers


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